HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$118+ Cheap flights from Madison (MSN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:15 amMSN - SJU
2 stops12h 07mUnited Airlines
Mon 12/152:05 amSJU - MSN
2 stops11h 39mUnited Airlines
Deal found 10/22$235
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
Tue 12/165:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/23$268
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:00 amMSN - SJU
2 stops22h 59mAmerican Airlines
Thu 12/114:41 pmSJU - MSN
1 stop9h 08mAmerican Airlines
Deal found 10/22$295
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:05 amMSN - SJU
1 stop12h 04mAmerican Airlines
Tue 12/165:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/22$298
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:30 amMSN - SJU
2 stops12h 56mUnited Airlines
Tue 11/182:20 pmSJU - MSN
1 stop10h 25mUnited Airlines
Deal found 10/21$314
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:13 amMSN - SJU
2 stops13h 56mAmerican Airlines
Mon 12/155:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/21$331
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:39 pmMSN - SJU
2 stops27h 26mAmerican Airlines
Tue 12/92:36 pmSJU - MSN
2 stops11h 04mAmerican Airlines
Deal found 10/22$340
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:20 amMSN - SJU
1 stop11h 32mAmerican Airlines
Thu 12/113:41 pmSJU - MSN
1 stop10h 08mAmerican Airlines
Deal found 10/22$357
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:59 amMSN - SJU
2 stops14h 21mDelta
Tue 1/133:55 pmSJU - MSN
1 stop8h 43mDelta
Deal found 10/22$358
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amMSN - PUJ
1 stop8h 47mAmerican Airlines
Sat 11/83:34 pmPUJ - MSN
1 stop10h 25mAmerican Airlines
Deal found 10/23$382
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/33:58 pmMSN - PUJ
2 stops19h 01mUnited Airlines
Sat 11/812:56 pmPUJ - MSN
2 stops9h 39mUnited Airlines
Deal found 10/23$409
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:38 amMSN - NAS
1 stop9h 05mDelta
Tue 12/95:08 pmNAS - MSN
1 stop6h 18mDelta
Deal found 10/21$445

Cheap flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated October 23, 2025.

Round-trip from

$235
(Delta)

One-way from

$118
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$407
From Madison Truax Field to Caribbean Islands
Search Deals
One-way flight from Madison Truax Field to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 23, 2025.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

12:38 pm-12:36 am

2 stops9h 58m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-12:03 pm

2 stops11h 58m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

6:15 am-3:20 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:38 pm

1 stop8h 43m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 2/14

2:48 pm-6:11 am

2 stops13h 23m

San Juan Luis Munoz Marin Intl

Wed 2/18

8:35 am-2:07 pm

1 stop7h 32m

$279

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 3/10

6:30 am-2:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-11:43 am

2 stops11h 38m

$320

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:05 am-2:01 pm

2 stops13h 56m

$325

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Mon 11/3

8:12 pm-4:24 pm

2 stops18h 12m

Punta Cana

Sat 11/8

3:34 pm-11:59 pm

1 stop10h 25m

$386

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Mon 11/3

3:58 pm-12:59 pm

2 stops19h 01m

Punta Cana

Sat 11/8

12:56 pm-8:35 pm

2 stops9h 39m

$409

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Tue 12/2

5:38 am-3:43 pm

1 stop9h 05m

Nassau Intl

Tue 12/9

5:08 pm-10:26 pm

1 stop6h 18m

$445

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sat 12/6

3:55 pm-10:19 am

2 stops17h 24m

Nassau Intl

Sat 12/13

12:07 pm-11:50 pm

2 stops12h 43m

$449

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Tue 12/2

8:12 pm-12:13 pm

2 stops15h 01m

Nassau Intl

Tue 12/9

12:07 pm-9:56 pm

2 stops10h 49m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, October is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $143). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $379). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to EPX?

Find hourly flight availability from Madison to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

A simple way to save on the total cost of your ticket is to fly from Madison to Caribbean Islands at noon. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated October 23, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Madison to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,982 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,995 reviews
Delta
7.9
Good
7,982 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,982 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Caribbean Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Caribbean Islands?

    A quick flight from Madison to Caribbean Islands can take about 7h 05m. United Airlines provides one of the quickest options available for as low as $235. There are 2180 mi between Madison and Caribbean Islands. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Madison to Caribbean Islands one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $118. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Madison to Caribbean Islands for a low price.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Punta Cana or Madison Truax Field - Saint Thomas Island Cyril E King, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Caribbean Islands?

    Currently, October is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $143). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $379). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Newark flights
O'Hare Intl to Orlando flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Fort Lauderdale flights
Minneapolis to Sky Harbor Intl flights
Minneapolis to John F Kennedy Intl flights
Minneapolis to Las Vegas flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
Minneapolis to Dallas/Fort Worth flights
Minneapolis to Cancún flights
O'Hare Intl to Atlanta flights
Minneapolis to Orlando flights
Minneapolis to Miami flights
O'Hare Intl to Dulles Intl flights
Minneapolis to LaGuardia flights
O'Hare Intl to Fort Myers flights
Minneapolis to Newark flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Seattle flights
O'Hare Intl to Ontario flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Santa Ana flights
Minneapolis to Denver flights
Minneapolis to Los Angeles flights
Minneapolis to Seattle flights
O'Hare Intl to Nashville flights
O'Hare Intl to Honolulu flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Boston flights
O'Hare Intl to Austin flights
Milwaukee to LaGuardia flights
Minneapolis to O'Hare Intl flights
Minneapolis to Fort Myers flights
Minneapolis to Tampa flights
O'Hare Intl to Hobby flights
O'Hare Intl to George Bush Intcntl flights
Minneapolis to Honolulu flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to San Diego flights

Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$254Average$663FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$651FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$633FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.